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The Synthesis Of N-Chlorosulfonyl Β-Lactams And Their Rearrangements, Lihua Zhang
The Synthesis Of N-Chlorosulfonyl Β-Lactams And Their Rearrangements, Lihua Zhang
Masters Theses
The synthesis of several N-chlorosulfonyl-β-lactams and their rearrangements have been carried out via CSI (chlorosulfonylisocyanate) reaction. The mechanism of β-lactam synthesis as well as its rearrangements were also studied. The characterization of β-lactams was performed with IR, 1H and 13C NMR, and HRMS. β-lactams 2-chlorosulfonyl-1-methyl-2-azabicyclo[4.2.0]octan-3-one (71), 1-chlorosulfonyl-4-methyl-4- (phenylmethyl)azetidin-2-one (74) and 1-chlorosulfonyl-4,4- (diphenylmethyl)azetidin-2-one (75) were synthesized for the first time. β-lactam 4-chlorosulfonyl-3, 9, 9-trimethyl-4-azatricyclo [6.1.0.03,6] nonan-5-one (73) was obtained as crystalline solid instead of liquid.
Different effects, such as temperature, solvents and catalysts, on the rearrangement of the …